Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.

Tech)

EXERCISE - 02
1. The decreasing of reactivity of the compounds given below towards solvolysis under identical conditions is:

(1) II > III > IV > I (2) I > II > III > IV (3) IV > III > II > I (4) III > II > I > IV

2. (A); Product (A) is :

(1) (2) (3) (4) None of these

3. (A); Product (A) is:

(1) (2) (3) (4)

4. In the reactions given below

R – Cl Product A

R – Cl Product B
the compounds A and B are :
(1) chain isomers (2) position isomers (3) functional isomers (4) metamers

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
5. Which is the major product expected from the following SN2 reaction?

Product

(1) (2) (3) (4)

6. Consider the following E1 /SN1 reaction:

The missing product(s) is (are):

(a) (b) (c) (d)

(1) a and c (2) c and d

(3) b and c (4) a ,b, c and d

7. Which of the following reactions does not represent major product?

(1)

(2)

(3)

(4)

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
8. Compare the two methods shown for the preparation of carboxylic acids:

Method 1:

+
Method 2:

Which one of the following statements correctly describes this conversion?

(1) Both method 1 and method 2 are appropriate for carrying out this conversion

(2) Neither method 1 nor method 2 is appropriate for carrying out this conversion

(3) Method 1 will work well, but method 2 is not appropriate

(4) Method 2 will work well, but method 1 is not appropriate

9. Which of the following statements is true?

(1) CH3CH2S– is a stronger base than CH3CH2O–

(2) CH3CH2S– is a stronger base but is less nucleophilic than CH 3CH2O–

(3) CH3CH2S– is a weaker base but is more nucleophilic than CH 3CH2O–

(4) CH3CH2S– is both a weaker base and less nucleophilic than CH 3CH2O–

10. In the given pair of alcohols, in which pair second alcohol is more reactive than first towards hydrogen Bromide.

(1)

(2)

(3)

(4)

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
11. Which product would be expected to predominate in the given reaction?

(1) (2) (3) (4) None of these

12. Which is the major product of the following reaction?

product

(1) (2)

(3) (4)

13. (A); Major product of this reaction is:

(1) (2) (3) (4)

14. Rate of SN2 reaction is :

(1) (B) > (A) > (C) (2) (C) > (A) > (B) (3) (A) > (B) > (C) (4) (A) > (C) > (B)

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
15. Among the given halides, which one will give same product in both SN1 and SN2 reactions.

(I) (II)

(III) (IV)

(1) (III) only (2) (I) & (II) (3) (I) (III) & (IV) (4) (I), (II) & (IV)
16. Which of the following is correct statement about CCl4
(1) CCl4 is used to extinguish fire under the name pyrene
(2) CCl4 resist to hydrolysis with boiling water due to non-availability to d-orbital in carbon
(3) CCl4 no ppt.
(4) All of these
17. In the given pair of compound, in which pair the second compound is more reactive than first forward S N2 reaction?

(1) (2)

(3) (4)

18. What is the major product obtained in the following reaction?

SNa + CH3 – Br Product.

(1) (2) (3) (4)

19.

Product (A) of the above reaction is:

(1) Ph – NH2 (2) Ph – CH2 – NH2 (3) Ph – CH2 – NH – CO2H (4) Ph – CH2 – NH – CHO

20. Identify C in the following series C3H7 I .

(1) (CH3)2CH – CN (2) CH2 = CH – CH2CN (3) Br – CH = CH – CN (4) CH2 = CH –

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)

21. Anisole Product

(1) (2)

(3) (4)

22. Which of the following compounds would react faster with NaCN in an SN2 reaction?

(1) (2) (3) (4)

23. What are the products obtained from the following reactions?

(1) (2)

(3) (4)

24. The back-side attack on 2-bromobutane by methoxide (CH 3O–) given the product shown below. Which Fischer projection
represents 2-bromobutane used as the reactant in this reaction?

product =

(1) (2) (3) (4)

25. Consider the following statements

(a) Bridgehead halides are inert to wards both SN1 and SN2 reactions
(b) The first step in both SN1 and E1 reactions is the same
(c) SN2 reactions proceed with total retention of configuration
(d) E2 eliminations are by the use of a solvent of low polarity and high concentration of a strong base
Which of the above statements are correct?
(1) a, b and d (2) a and c (3) b, c and d (4) a, b, c and d
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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
26. Consider the following alcohols:

The order of decreasing reactivities of these alcohols towards substitution with HBr is:
(1) III > I > IV > II (2) III > I > II > IV
(3) I > III > IV > II (4) I > III > II > IV
27. Benzotrichloride reacts with milk of lime to form:
(1) Benzal (2) Benzoic acid
(3) Benzyl alcohol (4) Phenol
28. Br – CH2 – (CH2)2 – CH2 – Br + CH3NH2  Product of the reaction is:

(1) (2) (3) (4)

29. 1-4-dichlorohexane (1 mole) + NaI (1 mole) Product of the reaction is:

(1) (2)

(3) (4)

30. HC  CNa + Cl – CH2 – CH2 – CH2 – I (A); Major product (A) is:
(1) H – C  C – CH2 – CH2 – CH2 – I (2) CH2 = CH – CH2 – I
(3) H – C  C – CH2 – CH2 – CH2 – Cl (4) CH2 = CH – CH2 – Cl
31. Alkyl halides can be obtained by all methods except:

(1) CH3CH2OH + HCl/ZnCl2 (2) CH3 – CH2 – CH2 – CH3 + Cl2

(3) C2H5OH + NaCl (4) CH3COOAg + Br2/CCl4
32. Which alkyl halide has maximum density?
(1) C3H7I (2) C2H5I (3) CH3I (4) CH3Br

33. ; Product (B) is

(1) (2) (3) (4)

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
34. In the given reaction

(A) is:

(1) C2H5OH (2) (3) CH3–CH2–CH2OH (4)

35. Which of the following compounds will not react by unimolecullar nucleophilic substitution mechanism–

I
CH3
(1) (C2H5)3CBr (2) (3) (4)

36. Which one of the following compounds is most rapidly hydrolysed by SN 1 mechanism–

(1) CH2=CH–CH2–Br (2) CH2=CH–Cl

(3) (C6H5)3CCl (4) C6H5CH2Cl

37. When benzyl chloride is treated with ethanolic KCN, large amount of benzyl ethyl ether is produced along with benzyl
cyanide. Therefore, the most likely mechanism for this reaction will be–

(1) SN2 (2) SN1

(3) both SN1 and SN2 (4) SN2’

38. Which one of the following compounds will react with water the fastest on heating–

(1) (CH3)3Cl (2) (CH3)3C–OTs

(3) (CH3)3CBr (4) (CH3)3CCl

39. Which one of the following compounds will be most reactive for SN 1 reactions–

(1) (2)

(3) (4)

40. When a mixture of CH3–CH2–CH2–Br and CH3COCH2Br is treated with NaI in acetone, then–

(1) The products are

(2) CH3COCH2Br reacts faster than CH3–CH2–CH2–Br

(3) CH3–CH2–CH2–Br reacts faster than CH3–CO–CH2–Br
(4) Both undergoes reaction at same rate as both are 1° halides

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)

Cl CH3
aq. OH
41. In the given reaction CH3O CH-CH-C NO2 major product [X] will be–

CH3 CH3

(1)

(2)
H

(3)

(4)

42. Which of the following nucleophile will show minimum reactivity towards SN 2 reaction–
 
(1) Me 3 CO (2) MeO


(3) (4) Me 2 CHO

43. In the given reaction [X], [X] will be–

(1) (2) (3) Mixture of a and b (4)

44. In the given reaction (A) and (B) will be–

(1) SO2 and HCl (2) SOCl2 and pyridine hydrochloride

(3) SO2 and pyridine hydrochloride (4) SOCl2 and HCl

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)

45. In the given reaction Cl will be replaced by OCH3 at carbon–

(1) 2 (2) 3 (3) 4 (4) any one of these

46. In the given reaction [X] will be–

(1) (2)

(3) (4)

47. In the following compound, arrange the reactivity of different bromine atoms toward NaSH in decreasing order–

(1) P > Q > R > S (2) S > Q > P > R (3) Q > S > R > P (4) P > S > Q > R
48. Consider the following reaction

Which of the following products is not expected to form?

(1) (2) (3) (4)

49. Find the major product of the following reaction–

(1) (2) (3) (4)

50. From each of the following pairs select the compound that will react faster with sodium iodide in acetone:
Pair-A- (1) 2- Chloropropane (2) 2- Bromopropane
Pair-B- (3) 1- Bromobutane (4) 2- Bromobutane
(1) 1, 3 (2) 1, 4 (3) 2, 3 (4) 2, 4
51. Which of the following molecules would have a carbon halogen bond most susceptible to nucleophilic substitution?
(1) 2-fluorobutane (2) 2-chiorobutane (3) 2-bromobutane (4) 2-iodobutane

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
52. Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halide due to -
(1) The formation of less stable carbonium ion (2) Double bond character due to resonance effect
(3) Longer carbon - halogen bond (4) The inductive effect
53. Which of the following compounds will be most reactive for SN 1 reactions?

Cl
Cl
Cl Cl
(1) (2) (3) (4)
CH3 CH3

54. Treatment of (CH3)3C.CH2OH with HCl gives:

(1) CH3–CH2–CH2–CH2–CH2–Cl (2)

(3) (4)

55. In the given pairs of alkyl-halide, in which pair the first compound is more reactive than second compound toward SN 2
reaction.
(1) (CH3)2CHBr or CH3 – CH3 – CH2 – CH2 – Br (2) CH3 – CH2 – CH2 – Br or CH3 – CH2 – CH2 – I
(3) Ph – Br or CH3 – CH2 – CH2 – Br (4) CH2 = CH – CH2 – Cl or H2C = CH – Cl
1
56. The compound which undergoes SN reaction most rapidly is:

(1) (2) (3) (4)

57. ; Product (A) of the given reaction is–

(1) (2) (3) (4)

58. Identify the principal organic product of the following reaction–

(1) (2) (3) (4)

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)

59. A; Product (A) of the reaction is–

(1) (2) no–reaction (3) (4)

60. (A), Product (A) in this reaction is–

(1) (2) (3) (4)

61. Arrange the following three chlorides in decreasing order towards SN1 reactivity.

(a) (b) (c)

(1) a > b > c (2) b > c > a (3) b > a > c (4) c > b > a
62. Arrange the following in decreasing order of nucleophilicity in ethanol medium:
F– (1) Cl– (2) Br– (3) I– (4)
(1) 1 > 2 > 3 > 4 (2) 3 > 2 > 1 > 4 (3) 4 > 3 > 2 > 1 (4) 2 > 3 > 1 > 4
63. Which among the following will undergo hydrolysis rapidly?

(I) (II)

(III) (IV)

(1) I (2) II (3) III (4) IV

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
64. Which one of the following undergoes nucleophilic aromatic substitution at the fastest rate–

(1) (2) (3) (4)

65. Which one of the following compounds undergoes E1 reaction most readily?

(1) (2) (3) (4)

66. In the reaction [X] is:

(1) (2) (3) (4)

67. In the given reaction as major product is:

(1) (2) (3) mixture (1) and (2) (4)

68. Consider the following reaction

Which of the following bases would give the highest percentage of

the product–

(1) (2) (3) CH3—CH2—OK (4)

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
69. Which alcohol, when heated with H2SO4 will undergo dehydration more rapidly–

(1) (2)

(3) (4)

70. Arrange the following bases in decreasing order with respect to the ratio of E2 elimination to SN 2 substitution products
expected when they react with isobutyl chloride–

(I) (II)

(III) (IV)

Select the correct answer from the codes given below–

(1) I > II > III > IV (2) II > I > III > IV
(3) IV > III > I > II (4) IV > III > II > I

71. In the given E2 reaction the transition state has–

(1) carbanion-like character (2) carbocation-like character

(3) Free radical character (4) Much like alkene character

72. In the given reaction Alkenes, number of alkenes formed will be–

(1) 1 (2) 2 (3) 3 (4) 4

73. In the given reaction [X] will be–

(1) CH3–CH2–CH=C=CH2 (2) CH2=CH–CH2–CH=CH2

(3) CH3–CH=CH–CH=CH2 (4) CH3–CH2–CH2–CCH

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
74. Identify the major product of following reaction–

(1) (2)

(3) (4)

75. A halide C5H11Br on treatment with alc. KOH give 2-pentene only. The halide will be:
(1) CH3 – CH2 – CH2 – CH2 – CH2 – Br (2)

(3) (4)

76. [X], [X] will be:

(1) (2)

(3) Both (1) & (2) (4) No product will form

77. Which of the following will undergo fastest elimination with alcoholic KOH?

(1) (2) (3) (4)

78.

(1) (2) (3) (4) No reaction

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
79. Match the column (I) and (II)

Column-I (Reaction) Column-II (Type of Reaction)

KSH
(a) R-2-chlorobutane (p) SN1
Acetone

EtO –Na +
(b) R-2-chlorobutane (q) SN2

(c) 2-bromo-2-methyl propane H2O (r) E1

H2SO4
(d) 2-butanol (s) E2

80. Select whether the following reagent combination will result in elimination or substitution reactions leading to the major
product.

Reaction

CH 3
| K+OC(CH3)3
(a) CH 3–C– Cl
| H2O
H

CH3
| H2SO4
CH3–C– OH
(b) |
CH3

Cl
(c) | alk. KOH
CH3–CH– CH2–CH3

CH3 + –
| NaN3
(d) CH3–C–
|
I
H

Cl
EtOH
CH3
(e)

CH3
| H2O
CH3–C– Cl
(f) |
CH3

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
81. Following molecules gives SN2 (yes or no)
Alkyl Halide 2-D Structure

(a) 1-Bromobutane
Br

(b) 1-Chlorobutane
Cl
Br
(c) 2-Bromobutane

Cl
(d) 2-Chlorobutane

(e) 2-Chloro-2-methyl propane

Cl
Br

(f) Bromocyclohexane

Br

(g) Bromobenzene

CH2–Br

(h) Benzyl bromide

(i) 1-Bromo-2, 2-dimethyl propane Br

(j) Bicyclo compound

Br

Br

(k) 1-bromotriptycene

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
82. If r1 & r2 are rate of reactions then match the following.
Column - I Column - II

(A) (p) Follows saytzeff rule

(B) (q) r1 r2

(C) (r) r1 > r2

(D) (s) r1 < r2

83. Encircle whichever of the following:

(a) undergoes an SN2 reaction more rapidly,

(b) undergoes an SN1 reaction more rapidly,

(c) undergoes an E2 reaction to give (Z)-1, 2-diphenylpropene:

(d) reacts with Nal to give (Z)-1,2-diphenylpropene:

(e) undergoes an SN1 reaction more rapidly,

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)
84. Encircle whichever of the following:

(a) undergoes an SN2 reaction more rapidly

(b) undergoes an E1 reaction more rapidly

(c) undergoes an SN1 reaction more rapidly

(d) undergoes an SN2 reaction more rapidly

(e) undergoes an E2 reaction more rapidly

85. Match the column :

Alkyl halide Relative rate (SN1) Relative rate (SN2)
(a) CH3–Br (p) 1 (w) 1200
(b) CH3–CH2–Br (q) 1.05 (x) 40
(c) CH3–CH–Br (r) 11 (y) 16
|
CH3
CH3
|
(d) CH3–C–Br
| (s) 1200000 (z) 1
CH3

86. Matrix:
Column-I (Compound) Column-II (Type of reaction)
Cl

(a) (p) SN1 reaction can taken place

Cl
(b) (q) SN2 reaction can taken place

Cl

(c) (r) SN1 is not possible

Cl
(d) (s) SN2 is not possible

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)

87. (A) (B), Product (B) is:

(1)

(2)

(3)

(4) None of these

88. tert-Butyl chloride reacts with an aqueous solution of sodium azide (NaN 3) to product tert-butyl azide by nucleophilic
substitution and tert-butyl alcohol by solvolysis, according to the following mechanism:

A B C
(a) If Br is substituted for Cl, the rate of the increase decrease not change

reaction will (encircle one)

(b) If Br is substituted for Cl, the azide : increase decrease not change

alcohol ratio will (encircle one)

(c) If the concentration of sodium azide is increased, increase decrease not change

the rate of the reaction will (encircle one)

(d) If the concentration of sodium azide is increased, increase decrease not change

the azide : alcohol ratio will (encircle one)

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 Alkyl halides and Aryl Halides MKA Sir (B.Tech, M.Tech)

ANSWER-KEY
Qus. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. 4 1 3 3 2 1 2 3 3 4 1 3 3 3 3 4 4 3 2 2
Qus. 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40
Ans. 3 4 2 4 1 1 2 2 4 3 3 1 3 3 4 3 2 2 1 2
Qus. 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Ans. 2 1 4 3 1 4 2 4 4 3 4 12 4 3 4 2 2 2 2 2
Qus. 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78

Ans. 2 3 1 1 4 3 2 2 4 3 1 3 3 2 3 4 1 2

79. (a – q), (b – s), (c – p), (d – r)

80. Substitution — d, f Elimination — a, b, c, e,
81. Yes – a, b, c, d, f, h No – e, g, i, j, k,
82. A-q, B-s, C-r, D-r

83. (a) CH3 – Br (b) (c)

(d) (e)

84. (a) (b) (c)

(d) (e)

85. a — p, w; b — q, x; c — r, y; d — s, z
86. a — r, s; b — p, q; c — r, s; d — r, s
87. 1
88. a — increase; b — not change; c — not change d — increase

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